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Investing After Retirement with Chuck Kramer
Chuck Cramer, an investor and entrepreneur, joins Avery on the show to discuss his journey into real estate investing post-retirement. After spending years in IT, Chuck talks about how he transitioned into real estate, starting with long-term rentals and eventually moving into short-term vacation rentals in Gatlinburg. His experience highlights the importance of reacting to market changes and making smart investment decisions after retirement.
Avery: Hey guys, welcome back to the show. Today we have Chuck Cramer, an investor and entrepreneur, and today we’re going to talk about investing.
Chuck: After retirement, a lot of our guests talk about how they’re maybe in the middle of their career or towards the beginning and they want to quit their job. But today we’re going to talk about starting investing after you’ve already retired.
Avery: So, how’s it going, Chuck? Tell us a little bit about yourself.
Chuck: Well, it’s going great. It’s not sunny, it’s raining, that’s a little different, but I spent 30 years in IT. Um, that’s kind of an understatement. I did a lot of different things as a senior IT guy. You have to know a lot about a lot of different kinds of businesses. I was sort of a virtual CIO for hire, gave me a lot of experience in a lot of different things, also gave me the opportunity to retire early at 53 without having yet invested in real estate. So, other than that, I’ve got some grandkids.
Avery: That’s awesome!
Chuck: Yeah, my kids are all spread across the country, and traveling is my number one passion.
Avery: Awesome. Yeah, the rain here is really bad, which is why my hair is a mess, Chuck, and I live in the same town. By the way, earlier I was walking into my office, and I was trying to walk through the landscaping because the road was kind of flooded, and I was trying to step through the pine straw because it looked like an island in the water, and I stepped in and went down into water up to my ankles. So, my socks and shoes are totally a mess, and I’m a mess, and um, yeah, it was an interesting start to the day. But let’s talk about, so, you haven’t always lived down here.
Avery: Let’s talk about your first short-term rental investment. What made you decide to do that? You’ve already retired, you’ve got grandkids, you’re spending time with your family. What made you decide to get into short-term rental investing?
Chuck: Well, as I said, my number one passion is travel. My wife and I wanted to do more of that, but one of the things that was kind of smarting was back in ‘08 when the markets took the big dive. I’m sitting there with my retirement account, I was on a 10-day cruise with no internet access, and I lost 28% during that cruise. It was a very expensive cruise. I decided I didn’t want to be in that situation again, so I only invested in things I could monitor frequently and react fast to. Well, after a few years, I kind of got tired of that and decided I didn’t want that real estate job calling me.
We started with a couple of long-term rentals, and they were working out well. We have family in Gatlinburg, so we made a trip up there around the time of the fires—the big wildfires in 2016—with the idea of investing in long-term rentals. We knew there was a housing shortage, and that was before the fire, and it met all my criteria for a market. We started looking at places, and back then almost everything for sale was a cabin, single-family, run-of-the-mill homes were pretty rare on the market. My agent goes, “You know, you can make a lot more money with this as a rental.” I said, “Yeah, but I don’t want to get involved with that.” But I looked at it, ran the numbers, and said, “He’s right. We can do like three times better.”
That became our first rental cabin. We paid cash for it, and it hasn’t stopped from there.
Avery: Well, I think you’ve bought and sold several over the years. So, how many cabins did you end up with after that?